


Dear Dean Winchester

by heyguysimbecca



Category: Dear Evan Hansen - Pasek & Paul/Levenson, Supernatural
Genre: Anxious!Dean Winchester, Dean Winchester Has Anxiety, F/M, Other, Other Additional Tags to Be Added, Songfic, Tags Are Hard, just read the preface, same, well kinda, you'll get it
Language: English
Status: In-Progress
Published: 2017-09-03
Updated: 2018-08-22
Packaged: 2018-12-23 05:38:00
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 4,388
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11983293
Author URL: https://archiveofourown.org/users/heyguysimbecca/pseuds/heyguysimbecca
Summary: The world didn't need Supernatural to meet Dear Evan Hansen. But when a lonely writer gets bored really late at night, the world gets Supernatural meeting Dear Evan Hansen.





	1. Preface

Hey guys! It's me. You know, the one who can never actually keep up with a story? Well, I'm working on it, for those who care.

Moving on, welcome to this new story called  _Dear Dean Winchester._ It's basically a story that takes place in the Supernatural universe with its characters and an OFC based on the plot of the storyline of the Dear Evan Hansen Original Broadway Cast Recording.

This will not be strongly based on the dialogue between the songs, because legally I haven't seen it.

;) 

Although, I might include Sincerely, Me: Reprise. Let's just see how the story is going at that point.

The idea is for every chapter to be based off of one of the songs, maybe including lyrics, or maybe just following the general idea of the song.

As of right now, this does not have an update schedule. So, if you're interested, please be sure to subscribe to this work or do something so you know when updates are posted. 

I do have good intentions for this story, I swear! 

So sit back, relax, and enjoy the story that is  _Dear Dean Winchester._

 

Hugs and butterfly kisses, 

~heyguysimbecca~


	2. Anybody Have a Map?

Dean Winchester always had self-destructive tendencies. His brother, Sam, knew this. He hated watching Dean tear himself apart because he thought he wasn't good enough for this reason or that reason or whatever nonsensical reason he had come up with that week. Sam wanted to help Dean. The only problem was that Dean didn't want to be helped. He wanted the best for others and he though the only way to achieve that goal was to humble himself to the point of self-loathing.

Abigale Greenwood was a hot mess. Scratch that, not even a hot mess. Just a general mess of a human being. She was terrible at taking care of herself. Everyone around her knew it. I would say all her friends knew it, but she really only had one friend. His name was Castiel. But, that doesn't mean that everyone else minded their own business. It seemed that everyone around her had cool, new self-care tips for her to try. She swore if she heard "drink more water" one more time, she was going to start throwing punches. 

And that is where this story begins. Dean Winchester: self-deprecating hunter. Abi Greenwood: normal 9 to 5 office job worker. Lives so different there's no way that one could even come in a thousand-mile radius of the other.

Yet, somehow...

~~~~~~~~~~~~~~

"Dude, that's, like, your-how many-six? Seven? How many drinks since this morning?" Sam said as he walked into the common area of the bunker to see that Dean had yet another new drink in his hand.

"Lost count. Six or seven sounds about right," Dean said groggily, not even looking up at Sam. He flipped a page in the book he was reading.

Sam started to walk toward Dean. "Okay. I'm just gonna..." He grabbed Dean's drink. Dean immediately snapped his head up. 

"Woah, woah, hey! Give that back!" Dean yelled, reaching for his drink. 

Sam pointed at Dean. "No. But while I have your attention, I've been wanting to tell you that I think you should stop drinking so much. It's not good for you and you're going to end up getting hurt."

"I'll be fine. Give me my drink," Dean complained, standing up.

"I'm walking away now," Sam yelled at Dean, his back turned toward him as he left the room, still with Dean's drink in his hand.

Sam had no idea what he was doing. He knew Dean was slowly killing himself and he didn't know what to do about it. He always looked like he had his life together when, in reality, he couldn't take care of himself, let alone his brother. But, he was trying as hard as he could to make his way through life without getting killed.

"Dean, I swear, one of these days, you're gonna kill me," he muttered as he walked to his room.

 

~~~~~~~~~~~~~~

_Knock. ... Knock._

"What do you want, Cas?" Abi yelled, knowing that her only friend was on the other side of the door.

"Can...I come in?" he asked slowly, unsure of himself. She grunted in affirmation. He slowly opened the door, poking his head inside. She was...a sight to behold. She was wearing an oversized t-shirt and sweatpants watching Netflix on her laptop and eating salt and vinegar chips. 

"Abigale, you should really take better care of yourself," Cas said, sitting down on the edge of her bed. She answered with some lame response, "yeah, okay," or "sure," or something of the sort. 

"Abi, I'm serious. Your health is terrible. You need to take better care of yourself." Cas had been trying to get her to put her health in higher priority for some time now. He knew how she was treating herself and he knew wasn't good for her. He had no idea how to make it better. 

"Please at least give me the chips. You shouldn't be eating them. You're not even hungry," Cas tried to find a happy medium with her. It was baby steps. Abi rolled her eyes and handed over her bag of salt and vinegar chips.

"Thank you, Abi. Please take care of yourself." The sound of wings fluttering told her that Castiel had disappeared.

"Yeah. Whatever."

Cas felt completely helpless. He wanted to help her but had no idea where to start. She was in terrible health, physically and mentally. He couldn't just heal her because she would just destroy herself all over again. He hoped she was actually going to start taking care of herself. 

~~~~~~~~~~~~~~

Wings fluttered. Cas appeared in the room.

"Hey, Cas," Sam said absently. 

"Hello, Sam." Castiel sat down opposite Sam in the library. "Can you help me with something?"

Sam put a bookmark in the book he was reading. "Yeah, sure. What's up?"

"Well, I have become acquainted with this girl. Her name is Abigale. I call her Abi. She hasn't been taking care of herself and I'm worried about her health. I don't know what to do about it. Do you happen to know what I should do?" Cas explained.

Sam scoffed. "Funny. I've been having the same problem with Dean. Yeah. No, I don't have any idea what to do. I was actually going to ask you about it, but obviously..." Sam trailed off, gesturing at Cas.

"Yes. I just hope this turns out all right. Good luck with Dean." Cas got up to leave.

"Good luck with Abi."

 

 

 

 


	3. Waving Through a Window

Some days, it was easier for Dean to just not do anything. Some days, all he had the energy to do was to lie in bed and stare at the wall for hours on end. Some days, Dean would get in the shower just so he could cry without being questioned.

Sam knew this. He knew that there were some days that, no matter how hard he tried, he couldn’t get a word out of Dean. He knew that he would need to step away for a while and let Dean battle whatever was going on in his head. He also knew about Dean’s habit of crying in the shower.

Sometimes, days went exactly like this one did.

“So, get this. There were a few deaths near here; it looks like a vamp nest, but I’m not quite sure. What do you think?” Sam said, turning his laptop toward Dean.

Dean glanced up at the screen absentmindedly. “Yeah, no. I don’t know either.” He continued to type away on his laptop.

Sam shifted in his seat. “Dude, seriously. I need your help on this one.” He pushed the computer closer to Dean.

“You’re probably right. It’s probably a vamp nest. We’ll head out later to go take care of it.” Dean didn’t even look up from his screen.

“Yeah,” Sam whispered, staring at Dean and wondering what was up with him. He knew Dean just wanted him to drop it, but he didn’t think he could.

~~~~~~~~~~~~~~

Cas had had enough. He couldn’t trust Abi on her own anymore. He needed to know that she was being taken care of, since she obviously couldn’t do it herself.

So, he did the only thing he could think to do.

He sent her to the Winchesters.

When she got home from work after a particularly rough day, she dropped all of her stuff by the door and went to her bed, landing face down and letting out a frustrated scream.

The sound of wings fluttering instantly made her feel better. She rolled her head to the side so her voice wasn’t muffled.

“Hey, Cas.”

She was met with silence.

“Cas?” She started to sit up, now slightly worried.

“I’m sorry, Abi, but I’m doing this for your own good.”

She immediately shot up because you knew that could only mean one thing.

Cas was about to do something stupid.

“Whoa, hey, slow down, what are you going to-” Cas placed two fingers on her forehead and she immediately dropped, now in a comatose state. He picked her up bridal style and left immediately for Kansas.

~~~~~~~~~~~~~~

Wings fluttered. Cas was in the kitchen of the bunker, holding Abi in his arms. No one was in the room, but he heard footsteps coming down the hallway.

“Cas, what’s-” Dean stopped talking as soon as he saw Cas. His eyes widened. “Who is that?”

“Where is Sam?” Cas asked desperately, frantically looking around.

“Okay, hold on. First, _who is that?”_ Dean tried to remain calm while trying to sort out everything in his head.

Alright. Cas just appeared in his kitchen holding an unconscious, at best, woman who appeared to be in business casual clothing. He had no idea who she might be; Cas had never talked about a woman before, but now he had to handle this situation.

“I will explain everything. I need to see Sam.” Cas paused. “Do you have a guest room?”

Dean couldn’t do anything but nod and start leading Cas toward the guest room. Cas followed, placing Abi on the bed when he got to the room.

Dean left to get Sam, and when they came back to the room, Sam had a similar reaction to the catatonic woman in their home.

“Who is that and why is she here?” Sam was trying not to freak out.

Cas sat on the end of the bed and looked at the woman on the bed. “This is Abi. She’s a friend of mine and she… actually, I’ll just let her explain.”

He placed two fingers on her forehead in the same manner as before. Abi immediately came to as if nothing had happened.

“-do because that sounds…” She trailed off. “Where am I?” she asked, slightly panicked, not taking her eyes off of Cas.

“Abigale, this is Sam and his brother, Dean. Sam and Dean, this is Abi.” Abi instinctively drew back from Sam and Dean.

Cas sighed he walked to Sam and Dean and started speaking under his breath. “Abi needs a place to stay for a while. She is a close friend of mine and I have reasons to believe that she is not safe living on her own anymore. I thought she could stay here until she is safe.”

Dean grabbed Cas' arm. “We need to talk outside. Now.” He sounded deadly serious.

Once they were outside, Dean began to chide Cas. “Dude, what are you doing? I don’t know her. How do I know she’s not making you do all of this to get to us? How do we know she’s not a demon or something?”

“Dean, I assure you, Abigale is a friend and I trust her. She is not making me do anything.” Cas explained patiently.

“Well, then, what’s she doing here? Why isn’t she safe on her own?” Dean asked, getting slightly annoyed that Cas was avoiding the elephant in the room.

“She’s destroying herself, Dean. She cannot take care of herself.” Cas was getting defensive because he knew that he couldn’t just take Abi back home. Not after all this.

“Well, she’s not staying here. Lots of people have that problem, Cas. You have to learn to live with it.” Dean walked away from the room. Cas stood outside the door, unsure of what to do.

Meanwhile, Sam had stayed in the room with Abi. They were both in shock.

“So, um, what’s...what’s happening?” Sam asked Abi, thinking she knew what was going on.

Unfortunately for both of them, she didn’t.

“No clue. Cas just came into my room when I got home from work today and said some crap about needing to do something for my own good, so I panicked and now I’m here. So, I know about as much as you do.”

Sam was confused. “But, Cas said you were in trouble or something.”

Abi looked at Sam in disbelief. “You’re kidding.”

Sam shook his head. “I’m not. Cas wants you to stay here.”

Abi fell back on the bed and groaned in annoyance. “I can’t do that. I don’t interact well with people. That’s why Cas thinks I need help.”

“You...feel like an outsider?” Sam questioned, trying to find out where she was going with this.

“I guess you could say that.” Abi sat up and Sam sat next to her.

“Tell me everything.”


	4. For Forever

Abi huffed as she thought of what to say.

 “I guess it all started just before I met Cas. I was in my last year of grad school. I didn’t have time to have friends. I spent most weekends in a little coffee shop just off campus.”

Sam smirked. “This sounds like the beginning of a bad rom-com.” He laughed and Abi snorted.

She covered her face with her hand. Sam took a mental note of that.

“Yeah. Well, anyway, Cas came into the shop one day. I didn’t think anything of it, you know, just a businessman or something headed into work. But he scanned the shop and started walking toward me. So, I was terrified, and when he finally got to me, I asked him what he wanted.”

“What _did_ he want?” Sam inquired.

“Well, he said some crap about being an angel of the Lord, so I punched him.”

Sam blinked. “You...you _punched_ him?”

“Yeah. I thought he was some crazy cult dude or something. Anyway, I found out later after many arguments, seeing a therapist, and passing out God only knows how many times, that he actually was an angel.”

Sam still looked dumbfounded. “Yeah, no kidding.”

“Yeah. But, I was never really, I don’t know, _religious,_ so it was hard to wrap my head around. He said he needed me for something, I don’t exactly recall what, but I’d agreed to help him, so he somehow arranged for me to live in an apartment, working a normal job, and I’d work with him as needed.

“But, it all felt so…” Abi did not have a way with words. “ _Lonely._ I was lonely. I couldn’t afford to have friends at work, because I would randomly disappear on occasion. My only friend was Cas, who always had some kind of responsibility. I started praying to him, and let me tell you, it’s weird to start praying after not doing it your whole life, but he never answered. I felt like there was always something I was missing out on, y’know?”

Sam was slowly nodding through her whole speech. “Yeah. Yeah, I get what you mean. It’s like, Dean sometimes gets into these moods where he won’t come out of his room for days, and Cas only answers to him, so I’m left alone. And all of our friends are dead, except Garth. No one’s quite sure what happened to him.”

Abi smiled. “I mean, there were some weekends where Cas would make time for me, and we’d go get frozen yogurt and climb trees and forget that there were responsibilities. Those were the best days.”

Sam mirrored her smile. “Sounds like it.”

Sam’s smile turned into a smirk. Abi stared back at him. “What’s that look about?”

Sam almost laughed. “I have an idea.”

“Which is?”

Sam stood and walked to the door. But, right before he walked out, he turned back.

 “Don’t worry about it.”


	5. Sincerely, Me

_Sam’s smile turned into a smirk. Abi stared back at him. “What’s that look about?”_

_Sam almost laughed. “I have an idea.”_

_“Which is?”_

_Sam stood and walked to the door. But, right before he walked out, he turned back._

_“Don’t worry about it.”_

~~~~~~

“Whatever that means,” Abi mumbled to the empty room. What was Sam up to?  


Sam walked into the kitchen. Cas was there. Perfect.

“Hey, Cas, do you think you can help me with something?” Sam asked, setting up his plan.

“That depends. What do you need?”

Sam proposed his idea to Cas, down to the last detail.

Cas stood up. “This sounds like a very poor idea. Do you know how many ways this could go wrong?”

Sam remained seated. “But what if it doesn’t? 

Silence fell across the room. Sam was waiting for Cas’ response. The silence was deafening and the tension could have crushed them.

“Fine. I will help you. But, to be clear, I’m doing this for Abi.  


Two quick knocks.

“Not now, Sam.”

The door opened anyway.

“I said, ‘not now’.” Dean hadn’t moved from his bed all day.

“I have something to tell you,” Sam explained, walking inside.

“What are we after and when do we need to leave?”

“It’s not that. Dean, you have a date tomorrow.” Sam was waiting for Dean’s reaction.

Silence.

Silence.

“I _what?_ ”

“I’m setting you up on a blind date. You need to leave the bunker. It’s not healthy.”

Dean was sitting on the edge of his bed, staring knives into Sam’s head. “Sam, when have I _ever_ cared about healthy?”

“You’re going to dinner with a girl tomorrow. You’re not getting out of this.”  


“Abi, can I talk to you?” Cas appeared in her room.

“Sure, what’s up?” She moved to the side so he could sit down next to her.

“I’m worried about you. That’s why I brought you here. I...I haven’t been able to be there for you and I’m worried about you being alone all the time.” Cas’ eyes never moved from hers.

“Cas, that’s sweet, but where is this coming from?”

"I was thinking, and I got some help from the Winchesters, but I set you up on a blind date."

Abi almost forgot to breathe. "You _what?_ "

"I set you up on a blind date. You're going to dinner with him tomorrow.”

“I can’t believe you right now.” Abi stood in frustration. She was about to go on a rant about how you couldn’t just set people up on blind dates without their consent, but she stopped herself.

What if it went well? What if he wasn’t complete trash?

“Fine. I’ll do it.”

Cas stood beside her. “I actually have a note from him, so you can know something about him before you go on your date.”

Abi took the envelope in surprise. “I guess I should write one back.”  
  
“Don’t worry. We’ve got it covered.” And Cas left.

 

Sam walked out of the room, but before he left, he set an envelope on Dean’s desk.

Dean stood and walked over to the desk. He hesitantly opened the envelope and sat down to read it. It read:

 

 _Dear whoever this may concern,_  

_I believe we’ve met before. You don’t know who I am, and I don’t know exactly who you are, but I’ve been informed that we’ve been introduced._

_I should tell you, this was not my idea. In fact, I was a little upset at first. But now, I have hope that this will end well._

_All you’ve got to do is just believe you can be who you want to be._

_Sincerely,_

_Me_

 

He read it over many times. This was real. This was actually a note from whoever he was going on a date with tomorrow. He tucked the note back into its envelope and set it back on his desk.

He hated to admit it, but he was excited.

 

Abi was freaking out. A blind date? And a note from the guy? This was too crazy.

With shaky fingers, she opened the envelope. The note read:

 

 _Dear whoever this may concern,_  

_I believe we’ve met before. You don’t know who I am, and I don’t know exactly who you are, but I’ve been informed that we’ve been introduced._

_I’m going to be honest; I’m freaking out. This is completely new territory for me. I don’t really do blind dates. I don’t really know much about them._ ~~_I only know about trees._~~

_All you’ve got to do is just believe you can be who you want to be._

_Sincerely,_ _  
_ _Me_

 

This couldn’t be real. This couldn’t be real. This couldn’t be real. 

This was real.


	6. Requiem

Abi was freaking out. How did this happen? How did she end up here?

  
Here, standing in the Bunker’s guest room, staring in the full-body mirror at her reflection clad in something other than a skirt and a blouse for the first time in months.

No, now she was in a dress, an actual dress, which Cas had to get for her, with her hair all done up and these godawful heels that she already knew she was going to hate.

_Whatever. You’ve never seen this guy before, and you’re probably never going to see him again. You can endure the pain of these friggin’ devil shoes for a few hours._

But that was just it, wasn’t it? What if actually went well? What if they actually saw each other again after tonight?

_Stop it. You’re getting ahead of yourself._

She, once again, looked into the mirror. She didn’t even know who was looking back at her. Over the course of the last couple of days, Abi had completely lost her old life. She didn’t show up to work, so that was probably a chapter of her life over. She hadn’t gone back to her apartment, so that was another chapter over.

She didn’t even know who she was anymore.

Abi did anything she could to keep her hands busy. Running her hands through her hair, wiping away wayward eyeliner, pulling down her dress, fidgeting with her necklace, running her hands around the band of her watch-

_Shit, is that the time?_

Abi ran rather unimpressively out the door, wobbling in her new heels, and tried not to break down in her car.

~~~~~~~~

Dean was done.

_Done._

He didn’t want to go. He didn’t want to get out of bed, get dressed up, and meet some random girl at some random place one time and never see her again.

Because that’s how blind dates worked. Someone thinks you and someone else would get along, and they set you up. You and the someone else go on one date, maybe two if you’re lucky, and then never see each other again.

Dean really, _really_ didn’t want to go.

But he did. He dragged himself out of bed with what little motivation he had left, he got dressed up, and he left to meet some random girl at some random place one time and never see her again.

Dean was like a toddler throwing a tantrum. He begrudgingly walked out the door, practically dragging his feet the whole way.

~~~~~~~~~

Dean arrived at the restaurant first. It was a cute little place, kind of hidden, but it had a nice atmosphere. Dean, still dreading the situation, got seated and waited for whoever was going to show up. Sam had told him that the girl was going to be wearing a blue sundress and white pumps.

_Blue sundress, white pumps._

_Blue sundress, white pumps._

_Dammit, man, why are you so nervous?_

_Deep breaths._

_Blue sundress, white pumps._

Dean waited five, ten minutes. He thought he’d been stood up, or something had happened, or there was a miscommunication, or _something_ , some sensible reason as to why she wasn’t there-

There.

Blue sundress, white pumps walked in the door, looked around, and seemed lost.

_No._

_They didn’t. They couldn’t have._

_...Right?_

“Abi?”

Abi spun around quickly. She immediately looked shocked.

“Dean? What are you, I mean, _why_ are you…”

“I think we’ve been set up, sweetheart.”

…

…

“Oh, _hell_ no.” Abi turned around, ready to leave, but her heel didn’t move, and she started to fall.

And guess who was there to catch her?

“Abi, wait,” Dean half-yelled as he reached out to catch her. She didn’t stand immediately, just...lingered there.

She seemed to come to her senses pretty quick and she jerked out of his arms and back onto her feet. “I’m going home. Screw all of this.”

“Abi, please, wait.” She paused, but didn’t turn around. “Cas is worried about you. You should stay with us.” There was a beat of silence. “And, we’re already here, and we have a table, so do you just, want to stay? Doesn’t have to be a date. But, I think, if you’re going to be staying with us, maybe we should talk a little.”

Abi took a deep breath. Slowly turning around, she responded. “Dean, this is crazy. I’m sorry, but I can’t...I can’t just...I’m just sorry.” Once again, she turned to leave. This time, Dean let her walk out the door. Out of his life.

He’d only just met her. Why was he so torn up about this? It wasn’t like actually knew anything about her.

It wasn’t like he immediately judged her to be a horrible person.

It wasn’t like he discovered that she wasn’t only after she walked out.

_Stop that, man. You’ve only known her a couple of days. She could still be a monster, for all you know._

_But she’s gone._

_You failed Cas._

_You failed_ her.

Dean hung his head, walking out of the restaurant and getting into his car. He pressed his forehead on the steering wheel and sighed.

_No chick flick moments._

Cas was going to be _pissed._

He sighed again, sat up, and began driving back to the bunker, sans Abi, much to everyone’s chagrin but her.

_How was this girl already messing with his head?_


End file.
